Winchester KY Homes for Rent
- Type:
- Single Family
- Sq.Ft.:
- 3,200
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.21 Acres
- Year built:
- 1910
- Baths:
- 3.00
- MLS#:
- 24020813
- Subdivision:
- Downtown
View additional info
Courtesy: Rector Hayden Realtors
859-276-4811
ADDITIONAL INFORMATION
Your chance to live in a beautiful, renovated home on historic Boone Avenue. Walk to downtown, the public library or college park. This two-story home has loads of renovations and is ready for you to move right in. This home features 4 bedrooms and a bonus room, currently used as an office. The updated kitchen is a cooks dream! Granite counters and huge island, newer appliances and backsplash. Large walk-in pantry. Lovely hardwood floors and beautiful re-tiled fireplaces make a perfect setting to entertain in the large dining room. Lots of room to spare and large bedrooms upstairs. Don't miss the sunroom, multiple decks & porches.
- Type:
- Single Family
- Sq.Ft.:
- 873
- Status:
- Active
- Beds:
- 2
- Lot size:
- 0.27 Acres
- Year built:
- 1975
- Baths:
- 1.00
- MLS#:
- 24020728
- Subdivision:
- Rural
View additional info
Courtesy: Kentucky Residential Real Estate, LLC
859-229-5974
ADDITIONAL INFORMATION
Nestled in the heart of rural Winchester, KY, this charming 2-bedroom, 1-bath home offers the perfect escape for nature lovers or those seeking a peaceful retreat. Surrounded by lush greenery year-round, the secluded property feels like a hidden gem, where you can enjoy the tranquility of the countryside. Inside, the cozy ambiance of a log cabin welcomes you, making it the ideal space for a starter home or a smart investment opportunity. Whether you're starting out or looking for a serene getaway, this property invites you to unwind and enjoy the simple beauty of country living.
$1,575,000
1120-1140 Bypass Road Winchester, KY 40391
- Type:
- Other
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 0.98 Acres
- Baths:
- MLS#:
- 24020722
- Subdivision:
- Commercial
View additional info
Courtesy: Block + Lot Real Estate
859-309-0099
ADDITIONAL INFORMATION
This unique offering can combine both properties into one sale as they are contiguous properties and owned by the same seller. Would be an effective way for a developer to acquire the 1140 Bypass Rd. property as an investment property, providing in-place income from Sleep Outfitters to help offset the development costs of the 1120 Bypass Rd. vacant lot.The seller is entirely open to independent sales of the two properties, or a collective sale. Contact agent for more details on the Sleep Outfitters Lease, and other questions.Property Highlights:- Traffic signaled lot- Bypass frontage- B-3 retail zoning- $90K NOI, 2-year term remaining- Utilities to site- Replaceable rental income at $18.75 PSF- Tenant responsible for all property expensesIdeally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart Shopping Centers.Winchester, Kentucky is the county seat of Clark County, Kentucky and is part of the Lexington-Fayette Kentucky Metropolitan Statistical Area. It is supported by such industries as Clark Regional Medical Center, Ale-8-One, and Catalent Pharmaceuticals.
- Type:
- Single Family
- Sq.Ft.:
- 2,994
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.21 Acres
- Year built:
- 1920
- Baths:
- 3.00
- MLS#:
- 24020622
- Subdivision:
- Downtown
View additional info
Courtesy: RE/MAX Elite Realty
859-408-7922
ADDITIONAL INFORMATION
Reduced for quick sale!! Don't miss out on your opportunity to own a 100+ year old home located near historic downtown Winchester, KY. The detail and charm located within the walls of this 2 story craftsman are what many dream of. Tall ceilings, fireplaces, in almost evey room, beautiful original wood work is abundant as you enter from the quintessential front porch that's perfect for casual nights or connecting with neighbors. A remodeled kitchen brings new flare & functionality to this early 1900s home and gives a great spot to make the meals to fill up the adjoining dining room. Pocket doors, original push light switches, a butler dummy , and so many features , sowell preserved remind us of times bygone. The front and rear staircases are just a few more mentions of items not typically recreated in modern homes. A 1st floor bedroom & full bath along with a laundry/mud room are welcomed functional bonuses to homes built in this time period! The second floor houses 3 additional bedrooms with 2 full baths for family or guests along with a sun room with small balcony that's perfect for relaxing and overlooking the rear yard. Brand new Dual zone HVAC system was recently added.
- Type:
- Other
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 0.81 Acres
- Baths:
- MLS#:
- 24020455
- Subdivision:
- Commercial
View additional info
Courtesy: Block + Lot Real Estate
859-309-0099
ADDITIONAL INFORMATION
Rarely available Bypass frontage lot for sale! Exciting opportunity to locate alongside a new Chipotle that is soon to be under construction. Retention in place, leaving approximately 1/2-acre developable. Perfect location for a national retailer.Ideally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart shopping centers.Winchester, Kentucky is the county seat of Clark County, Kentucky and is part of the Lexington-Fayette Kentucky Metropolitan Stastistical Area, and is supported by such industries as Amazon, Ale-8-One, and Catalent Pharmaceuticals.Property Highlights:-Utilities to site-Bypass frontage- B-3 retail zoning- Water retention in place
- Type:
- Single Family
- Sq.Ft.:
- 4,600
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.46 Acres
- Year built:
- 2002
- Baths:
- 4.00
- MLS#:
- 24020327
- Subdivision:
- Fairway Woods
View additional info
Courtesy: Tom Goebel & Company
859-744-3637
ADDITIONAL INFORMATION
Motivated seller! This is the one that you've been waiting for! Remarkable attention to detail was clearly taken in the building of this home. This stunning 4 bedroom, 4 bath home is located on a quiet cul de sac overlooking Southwind Golf Course. Walk in the front door to an inviting two story foyer and beautiful hardwood floors. The great room is amazing with beautiful windows that overlook the golf course. The great room opens to the gourmet kitchen with quartz countertops and back splash and walks out to the deck also overlooking the golf course. The dining room has tray ceilings and gorgeous crown molding. The primary suite is located on the first floor along with 2 other spacious bedrooms. The second floor bonus room could also be used as a bedroom. In the lower level you will find a full service kitchen, bedroom, living room with custom built in bookshelves. On the lower level you will also find tons of storage with a storage room and a garage. The custom wood and crown molding throughout is extraordinary. Set up your viewing of this fabulous home today. Please allow 24 hours notice to view.
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 6.96 Acres
- Baths:
- MLS#:
- 24020143
- Subdivision:
- Rural
View additional info
Courtesy: United Real Estate Bluegrass
859-800-7355
ADDITIONAL INFORMATION
Looking for a bit of privacy?....Here is 6.9586 +/- acres cleared and ready to build, approx 4 acres is fenced, new driveway culvert put in with approx 878'+/- of road frontage. Buyer to verify sq footage, road frontage on 2 sides, and acreage.
- Type:
- Single Family
- Sq.Ft.:
- 2,030
- Status:
- Active
- Beds:
- 4
- Lot size:
- 5.11 Acres
- Year built:
- 2012
- Baths:
- 2.00
- MLS#:
- 24020193
- Subdivision:
- Rural
View additional info
Courtesy: Woods Realty Group
859-644-5077
ADDITIONAL INFORMATION
Are you looking for your peace and quiet in the country? Then this is your new home! Get ready to enjoy what this 5 plus acre property has to offer. There is both cleared and wooded land. This property also has water access that is not in a flood zone. There is a spring fed watering pond and a wet weather creek. The property is partially fenced, and offers a small stock barn, two loft shed, and a chicken coop. The perfect home for a beginning, modern day homesteader!!! Schedule your private showing today!!
$145,000
31 Vine Street Winchester, KY 40391
- Type:
- Single Family
- Sq.Ft.:
- 1,443
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.16 Acres
- Year built:
- 1950
- Baths:
- 1.00
- MLS#:
- 24019973
- Subdivision:
- Rural
View additional info
Courtesy: EXP Realty, LLC
888-624-6448
ADDITIONAL INFORMATION
Discover the perfect opportunity with this 3-bedroom, 1-bathroom house in the heart of Winchester! Whether you're a homeowner ready to put your personal touch on a cozy space or an investor seeking a promising flip or rental property, this home has everything you need to make it shine. Newer roof and HVAC!!
- Type:
- Single Family
- Sq.Ft.:
- 2,090
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.25 Acres
- Year built:
- 1970
- Baths:
- 3.00
- MLS#:
- 24019933
- Subdivision:
- Holiday Hills
View additional info
Courtesy: Kentucky Residential Real Estate, LLC
859-229-5974
ADDITIONAL INFORMATION
You must see this lovely brick home on a basement in Holiday Hills! If you like pickleball, disc golf, or anything else Wiseman Park has to offer, you will love this convenient location! 3 bedrooms, 2 and a half baths. Very practical kitchen featuring granite countertops and a brand new refrigerator. Plenty of room for entertaining with a beautiful deck just off the open concept kitchen / dining room / family room combo. Good sized den and workshop / storage area in the partially finished walk out basement with attached garage. Storage shed with electric in the fenced in back yard. You need to see this one!
$404,900
520 Bailey Lane Winchester, KY 40391
- Type:
- Single Family
- Sq.Ft.:
- 2,400
- Status:
- Active
- Beds:
- 4
- Lot size:
- 24 Acres
- Baths:
- 3.00
- MLS#:
- 24019867
- Subdivision:
- Rural
View additional info
Courtesy: RE/MAX Creative Realty
859-422-2000
ADDITIONAL INFORMATION
Beautiful large ranch completely remodeled on 24 acres. large bedrooms, family room, dining room, formal living room, 4 Bedroom and 3 baths. 30 foot above ground pool multiple outbuildings, front porch large back patio and just minutes from downtown Winchester. All new Bathrooms, All new Kitchen, All new fixtures, All new flooring. All new paint. House is situated on a quiet dead end lane. 24 acres to use how you see fit. Pasture, hunting, off grid, multi-family just depends on what your are looking for.
- Type:
- Single Family
- Sq.Ft.:
- 2,470
- Status:
- Active
- Beds:
- 3
- Lot size:
- 5 Acres
- Year built:
- 2012
- Baths:
- 2.00
- MLS#:
- 24019381
- Subdivision:
- Rural
View additional info
Courtesy: Tru Life Real Estate
859-785-1986
ADDITIONAL INFORMATION
Charming 3-bedroom, 2-bath home on 5 acres with beautiful views, featuring new flooring throughout. This property is full of life, with abundant wildlife and a variety of fruit-bearing trees, including 2 apple trees, 2 peach trees, 2 pear trees, a grapevine, blackberry bushes, and walnut trees. There's also a chicken coop, a goat enclosure, and a fenced yard, providing ample space for all your needs. The spacious 30x40 garage offers plenty of room for storage or hobbies. Located in Mt. Sterling, with the benefit of Clark County schools and property taxes. This one-level home also includes a small outbuilding, and the dog house is equipped with heating and cooling for your pets' comfort. Ideal for those seeking country living with modern amenities.
- Type:
- Single Family
- Sq.Ft.:
- 2,361
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.83 Acres
- Year built:
- 1945
- Baths:
- 3.00
- MLS#:
- 24018997
- Subdivision:
- Rural
View additional info
Courtesy: Keller Williams Commonwealth
859-721-2121
ADDITIONAL INFORMATION
NEW PRICE REDUCTION!!! This Is The One You Have Been Waiting For!!! This Completely Remodeled 4 Bedroom 3 Bathroom Home On An Unfinished Basement Has It All. Features Include An Open Floor Plan; Dining Room With Fireplace; Big Kitchen With Lots Of Cabinets; Granite Tops; Stainless Steel Appliances; Range Hood; Farmhouse Sink; Huge Laundry Room Off Kitchen/Master Bedroom; First Floor Master Bedroom With Fireplace And Master Suite With Soaker Tub And Full Tile Shower; Large Bedrooms; Lots Of Space And Loads Of Storage; Garage; Man-Cave/She-Shed; Absolutely Beautiful Lot And Diamond Location.
- Type:
- Single Family
- Sq.Ft.:
- 1,780
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.31 Acres
- Year built:
- 1950
- Baths:
- 2.00
- MLS#:
- 24018875
- Subdivision:
- Victory Heights
View additional info
Courtesy: ListWithFreedom.com
513-505-5222
ADDITIONAL INFORMATION
Fully renovated in 2023, 3 bed X 2 bath, new landscaping in 2024, includes a basement, detached garage, shed, gas stove and fireplace, & 2nd floor vaulted ceilings.
- Type:
- Single Family
- Sq.Ft.:
- 2,384
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.21 Acres
- Year built:
- 2004
- Baths:
- 3.00
- MLS#:
- 24018742
- Subdivision:
- Oakmont
View additional info
Courtesy: Ensor Real Estate, LLC
859-749-0892
ADDITIONAL INFORMATION
OPEN HOUSE, Sunday, September 15, hours 1-3Happiness is this two story home with lots of room, great corner lot, large patio for entertaining and grilling, great room, master bedroom with large closet, close to shopping, schools, hospital, restaurants, double garage, located on a cul-de-sac, call today!
- Type:
- General Commercial
- Sq.Ft.:
- 1,800
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 0.1 Acres
- Baths:
- MLS#:
- 24018626
- Subdivision:
- Commercial
View additional info
Courtesy: Block + Lot Real Estate
859-309-0099
ADDITIONAL INFORMATION
Located in the heart of Downtown Winchester, KY in the Court House Square, this space has been used as office space for a number of years, but is also conducive to a retail storefront use. The space features three large offices, 2 bathrooms, and the new owners of this building have already put a considerable amount of work into this beautiful building and are currently renovating the top three floors and exterior. Winchester First is offering numerous grants to help incentivize you to bring your business to Winchester!Property Highlights:- Recently renovated space with ongoing building renovations- Located in Downtown Winchester in the Court House Square, a sought-after area- Winchester First is offering numerous new business grantsWinchester, KY is conveniently situated just 18 miles East of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, Engine House Pizza, La Trattoria, Loma's, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown!
- Type:
- Single Family
- Sq.Ft.:
- 4,665
- Status:
- Active
- Beds:
- 4
- Lot size:
- 1.64 Acres
- Year built:
- 1993
- Baths:
- 4.00
- MLS#:
- 24018605
- Subdivision:
- Rural
View additional info
Courtesy: Freedom Realty & Property Management
859-771-0777
ADDITIONAL INFORMATION
Recent price reduction has this home price at $139 per finished square foot. This is not counting extra basement space and attic space. When you enter this amazing custom-built home, you will feel at home. A multitude of incredible amenities, it's hard to even know where to start, we will begin in the kitchen that received a massive update in 2020 that included quartz countertops and backsplash, some new cabinets, new flooring, as well as new lighting and appliances. Next let's move to the basement that features an amazing entertainment area that has an overhead projector and large screen for family movie nights. You can enjoy your morning coffee on the beautiful covered back patio with brick walls and posts that overlooks a big back yard and a pond that's on the adjoining property making you feel as if you are deep in the country instead of being a little over a mile from the bypass. You will notice the plumbing and electric has been completed to a high-level in this home. 4,600 sq. ft finished plus 900 unfinished in basement and 800 in floored attic. All information is believed to be accurate. Buyer to confirm.
$369,900
206 Jett Drive Winchester, KY 40391
- Type:
- Single Family
- Sq.Ft.:
- 1,635
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.23 Acres
- Year built:
- 2024
- Baths:
- 2.00
- MLS#:
- 24018286
- Subdivision:
- Creekside
View additional info
Courtesy: Ensor Real Estate, LLC
859-749-0892
ADDITIONAL INFORMATION
New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75, Lexington, Richmond, shopping, churches, hospital and schools, pictures to follow as home is being constructed.
$359,900
210 Jett Drive Winchester, KY 40391
- Type:
- Single Family
- Sq.Ft.:
- 1,600
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.42 Acres
- Year built:
- 2024
- Baths:
- 2.00
- MLS#:
- 24017675
- Subdivision:
- Creekside
View additional info
Courtesy: Ensor Real Estate, LLC
859-749-0892
ADDITIONAL INFORMATION
Don't miss out on this wonderful ranch floor plan, New Construction, 3 bedrooms, 2 baths, covered porch, great location, Call today.Size of home may vary from plan, spec home,all specifics have already been ordered. This information will follow within a few weeks and posted on line.
- Type:
- General Commercial
- Sq.Ft.:
- 31,200
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 5.24 Acres
- Year built:
- 1962
- Baths:
- MLS#:
- 24017433
- Subdivision:
- Commercial
View additional info
Courtesy: Block + Lot Real Estate
859-309-0099
ADDITIONAL INFORMATION
Located at the 96 Exit of I-64, this property sits on over 5 acres and has two large buildings and over 2 acres of paved parking. The main building was most recently used as a car dealership. Lots of updates to the interior and exterior of the property. The main building has numerous offices and two large areas for auto repairs. The back building has 18' clear ceiling heights and two large overhead doors. Owners will also consider a ground lease.Property Highlights:- Highly visible and accessible off Exit 94 of I-64- Recently renovated with updates to the interior and exterior- Versatile building spaces conducive to multiple uses: industrial and/or retail
- Type:
- Single Family
- Sq.Ft.:
- 972
- Status:
- Active
- Beds:
- 2
- Lot size:
- 0.23 Acres
- Year built:
- 1940
- Baths:
- 1.00
- MLS#:
- 24017233
- Subdivision:
- Thomson Addition
View additional info
Courtesy: Ensor Real Estate, LLC
859-749-0892
ADDITIONAL INFORMATION
You must view this adorable remodeled home located in a convenient location, charming, large back yard, walk to downtown Winchester, close to college park, make sure you view this one today! Sentri lock is on the back door, parking in rear allley access
- Type:
- Single Family
- Sq.Ft.:
- 3,200
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.27 Acres
- Baths:
- 4.00
- MLS#:
- 24016751
- Subdivision:
- Thomson Addition
View additional info
Courtesy: RE/MAX Creative, Winchester
859-422-2000
ADDITIONAL INFORMATION
As you enter the colonial-style home, you're met with a foyer that sets the tone for the home's timeless charm. The welcoming floor plan invites you to the formal dining room or great room on each side, perfect for hosting. The kitchen features beautiful custom-built maple cabinets. Continue into the cozy living room & breakfast nook, where French doors open to a screened-in porch & an expansive deck, providing the perfect spot for enjoying morning coffee. Off the great room, you'll find the first of two primary bedroom suites.. The second is on the second floor, complete with a kitchenette for convenience. Also you'll find a third full bath, a bedroom with a large custom-built armoire and a 4th bedroom that being used as a laundry room. The nearly 1200 sqft basement holds incredible potential, featuring a fireplace & kitchenette. Whether you envision it as additional living space or a vast storage area, this clean & dry basement is a blank canvas ready for your ideas. With its generous room sizes and top-quality craftsmanship, this home offers both luxury and practicality in the heart of Winchester's historic Thomson Additio
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 2.34 Acres
- Baths:
- MLS#:
- 24016652
- Subdivision:
- Rural
View additional info
Courtesy: eXp Realty, LLC
859-721-2127
ADDITIONAL INFORMATION
Welcome to 12651 Ironworks Rd in Winchester, KY! This residential lot offers a wonderful opportunity to build your dream home in a tranquil setting. With the perfect mix of country living and convenience, you'll be just 15 minutes from both downtown Winchester and Mt. Sterling. Easy access to the Bert T. Combs Mountain Parkway makes this property ideal for those who want a peaceful retreat while staying connected to nearby amenities. Don't miss out on this prime building opportunity--make 12651 Ironworks Rd yours today!
- Type:
- Land
- Sq.Ft.:
- n/a
- Status:
- Active
- Beds:
- n/a
- Lot size:
- 1.72 Acres
- Baths:
- MLS#:
- 24016649
- Subdivision:
- Rural
View additional info
Courtesy: eXp Realty, LLC
859-721-2127
ADDITIONAL INFORMATION
Welcome to 12591 Ironworks Rd in Winchester, KY! This residential lot offers a fantastic opportunity to build your dream home in a serene setting. Enjoy the perfect blend of country living with the convenience of being just 15 minutes from both downtown Winchester and Mt. Sterling. With easy access to the Bert T. Combs Mountain Parkway, this lot is ideally situated for those seeking a peaceful retreat with nearby amenities. Don't miss out on this prime building opportunitya'make 12591 Ironworks Rd yours today!
- Type:
- Single Family
- Sq.Ft.:
- 2,484
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.92 Acres
- Year built:
- 1987
- Baths:
- 3.00
- MLS#:
- 24016460
- Subdivision:
- Calmes Estates
View additional info
Courtesy: 5.23 Real Estate
859-428-7960
ADDITIONAL INFORMATION
Rare Ranch on a Basement! Sitting on almost an acre, this is the perfect home to bring your pets. A large portion of the backyard is already fenced with room for a pool, fire pit AND MORE. Come inside to enjoy the main level. Boasting a complete house with 3 bedrooms with 2 bathrooms, a kitchen with dinning area, and a large living room. Downstairs in the Walk-Out Basement you will find an oversized room ready for your enjoyment. The basement also includes a large flex room that is currently used for a 4th bedroom and a full bathroom with large soaker tub.
The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Lexington Bluegrass Multiple Listing Service. The Broker providing this data believes them to be correct but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2025 Lexington Bluegrass Multiple Listing Service. All rights reserved.
Winchester Real Estate
The median home value in Winchester, KY is $238,250. This is higher than the county median home value of $206,000. The national median home value is $338,100. The average price of homes sold in Winchester, KY is $238,250. Approximately 52.42% of Winchester homes are owned, compared to 38.21% rented, while 9.38% are vacant. Winchester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today!
Winchester, Kentucky has a population of 18,993. Winchester is less family-centric than the surrounding county with 25.63% of the households containing married families with children. The county average for households married with children is 25.74%.
The median household income in Winchester, Kentucky is $47,034. The median household income for the surrounding county is $59,294 compared to the national median of $69,021. The median age of people living in Winchester is 36.9 years.
Winchester Weather
The average high temperature in July is 85.8 degrees, with an average low temperature in January of 22 degrees. The average rainfall is approximately 45.8 inches per year, with 9.4 inches of snow per year.